Methyl 5-nitropicolinate → Methyl 5-aminopyridine-2-carboxylate

HRID 980540Notes

Reaction equation

HRID 980540 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 12457882Methyl 5-nitropicolinateHCID 178418361HCID 178418361, compound

Product 1

HCID 12457877Methyl 5-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 10 g methyl 5-nitropicolinate in 400 ml ethyl acetate is stirred under hydrogen in the presence of 1 g platinum oxide at room temperature and atmospheric pressure. When no further hydrogen uptake occurs, the catalyst is removed by filtration, the filtrate concentrated, and the product collected. This is recrystallized from ethyl acetate to give analytically pure methyl 5-aminopicolinate, mp 147°-150.5° C.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated
  3. customthe product collected
  4. customThis is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-684069c36771475991cba57b57997486
Source dataset
uspto-grants-1987_01
Patent number
US04638068

Reaction notes

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